


How I met your father

by n_nami



Category: Supernatural
Genre: How I met your mother!AU, M/M, Rom-com, Romantic Comedy
Language: English
Status: Completed
Published: 2013-04-28
Updated: 2013-04-28
Packaged: 2017-12-09 20:02:22
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 19,415
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/777452
Author URL: https://archiveofourown.org/users/n_nami/pseuds/n_nami
Summary: <blockquote class="userstuff">
              <p>Dean is in his late twenties and searching for someone to settle down with. Meanwhile, Sam and Jess are on their way to getting married. Last one of the group is Gabriel, loving pranks, laser tag and messing with Dean's head - who struggles with his sexuality when he meets a certain blue-eyed man.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> I began writing this for the deancasbigbang 2012, but ended up with writer's block. I chose and finished writing a different story for the bigbang in the meantime, but there was this WIP laying around on my hard drive, teasing me. So I finished it.
> 
> Warning: this story is un-beta'd. All mistakes are mine.
> 
> Originally posted [here](http://www.fanfiction.net/s/8371275/1/How-I-met-your-father).

**The year 2030**

_"Kids, I'm gonna tell you an incredible story. The story of how I met your father."_

_"Are we being punished for something?"_

_"No."_

_"Yeah... is this gonna take a while?"_

_"Yes!"_

_The kids – a dark-haired girl who just turned 16 and her 14-year-old brother, a blonde boy with Dean's green eyes – roll their eyes._

_"25 years ago, before I was dad, I had this whole other life. -_

_"In the fall of 2005, I was living in California where I just had taken a new job as a mechanic. I was sharing an apartment with your aunt Jess and your uncle Sam, who had just started Law School at the time, and I was working to support him. Anyway, my life was good - until your uncle Sam screwed the whole thing up-"_

**The year 2005**

Sam knelt on one knee in front of Dean on the living room floor. "Will you marry me?"

"Ugh, Sam, I'm getting cavities here. Or spontaneous breast growth. Of course she will," Dean said, pushing past his brother and heading for the kitchen of their shared apartment. He got two beers out of the fridge and handed one of them to Sam before he removed the cap of his own.

"Cheers, Sammy," Dean said with a sincere smile, dropping the sarcasm. "It is kinda scary to know you will be engaged by tonight," he added, not meeting Sam's eyes.

"Yeah, tell me about it," Sam huffed, fidgeting with the label of his bottle after opening it and drinking a first mouthful. "Anyway, I'm perfectly prepared. Got everything I need to cook up some pasta and a bottle of champagne-"

"So that's why I support you?" Dean asked back with a smirk playing around the edges of his lips. When Sam began to pout, he backtracked quickly. "Dude. Special occasion. It's not like I'm serious, geez."

Sam rolled his eyes. "What are you going to do tonight, then?"

_So what did I do? Right. Call your uncle Gabriel._

"Heya, Dean-o, whaddup?" Cheery mood always meant Gabriel A) had just gotten laid or B) was about to. Both options let Dean roll his eyes.

"Hey Gabe. You wanna do something tonight?"

"Yeah, sure. Meet me at the bar at six. Oh, and Dean?"

"Yeah?"

"Suit up!"

Dean rolled his eyes again and hung up on Gabriel.

That night at the bar, the two of them stood idly by the counter, where Ellen shuffled around busily after handing them each a beer. Gabriel, of course, wore a suit and tie.

"Dean, where's your suit? Will you just once listen to me?" Gabriel asked and shook his head in disapproval.

"You don't really expect me to answer that, do you?" Dean flipped him off.

"Dude-"

"Gabe, save it, okay?" Dean shot back good-naturedly, staring into the distance and ignoring Gabriel's unnerved gaze at him.

"So Sammy's getting engaged tonight, huh?" Gabriel asked after a few moments of awkward silence.

"Yeah," Dean drawled out, "and he isn't even thirty." He huffed out a short laugh.

"God, yes. Kiddo is crazy," Gabriel shook his head in disbelief and took a sip from his bottle. "And there I always said: Never think about getting married until you're at least thirty!"

"It's kind of weird, you know," Dean said thoughtfully. "It's always been Dean and Sam and Jess, and now it'll be Sam and Jess and _uncle_ Dean or some shit like that."

Gabriel snorted amused.

"Don't laugh at me, you'll be uncle Gabe then," Dean grinned at Gabriel's screwed-up face at that. "'Sides, my baby brother is getting engaged tonight, so don't hold it against me that I'm getting sentimental." Dean elbowed Gabriel into his side.

The shorter man just quirked an eyebrow at Dean. "Seriously, dude? You need some distraction. And, as your best friend," - he ignored Dean's groan and eye-roll at that - "I suggest we play a little game I like to call _Haaaave you met Dean_?"

"No, Gabe, we won't play _Have you-_ "

Within a split second, Gabriel had turned around and tipped on the shoulder of a cute little blonde with some stunning curves. Needless to say that Dean had been drooling over her at first sight. "Hey, have you met Dean?" and with that, he was off the radar and probably hitting on some hot guy.

She turned around, and Dean was a bit shell-shocked when he first saw her beautiful eyes and curly blonde hair framing it and the delicious swing of her lips- "Hello, uhm... Dean," he said, at a loss for a better phrasing.

She tilted her head to the side and grinned brightly. "Jo," she said simply. They shook hands, which was followed by a few seconds of awkward silence.

"You wanna go sit?" she added quickly with a finger pointed at an empty table.

"Sure," Dean said, winking before he took the lead and made a beeline for the booth.

"So, how are you? What brings you here tonight?" Jo asked with a friendly smile on her lips.

"Oh, I'm living upstairs, so... I'm pretty much here every evening. And as for today, I was ordered to leave the apartment so my brother could take his time and propose to his girlfriend," Dean chuckled, "It's a bit surreal at the moment, my little brother tying the knot and everything, while I'm still- yeah well. Sorry, I'm just a bit worked up," he said, avoiding Jo's eyes and picking at the label of his bottle.

"I understand, don't worry," she said, grinning and taking a sip from her drink. "You planning on marrying some day?"

"Sure," Dean nodded without having to ponder, and deadpanned, "just gimme the girl first, _then_ we can talk."

She raised an eyebrow. "You seem kinda bitter about this."

Dean huffed. "Huh. The operative word being _kinda_. It's not like I'm jealous or anything, it's just that I'm having this image of a house and a wife and one-point-four kids, and it's just a bit depressing to notice that I have none of it achieved so far. My brother's four years younger than me and he's straight on his way to that," he said. Then, quieter, "Sorry, I sound pathetic, don't I?"

Jo chuckled. "Yeah, you do, Dean. Don't worry about it. I think it's adorable."

Managing a little smile, Dean blinked surprised at her. "Thanks. Say... you wanna go out sometime?"

"Uhm," Jo answered, glancing at the bar. "You know that Ellen is my mom, right?"

"Oh. Oooh," Dean said. "Uh-oh."

Jo just grinned some more. Dean liked her, but sooner or later, the conversation ended and Dean found himself back at the bar, at Gabriel's side. So much for that. There was no way – _no way_ – Dean was going to hit on Ellen's daughter. Because despite how much he liked Ellen as a bartender, she... well, let's just say, Dean wasn't so sure about having her as his mother-in-law. Her usual mother-hen-behavior around Sam and Dean was enough as it was.

"You know," Dean said to Gabriel, trying not to sound too desperate, "even if, by any chance, I'd be ready to get a girl and marry and have kids – which I'm not so sure about, just for the record - just one question: Where the hell she?"

_And right there, across the room, I saw him._

_He had dark brown hair, a five o'clock shadow on his cheeks and stunning, deep blue eyes. You know, kids, when you meet someone, sometimes you've got that feeling that time stands still and you're like 'wow, he she/he is hot, I wanna have sex with him/her'. Imagine that, plus a lot of unexpected feelings. The kind where you just think 'Hey, see that guy/girl? Yeah, I'm gonna marry him/her.'_

So Dean said to Gabriel, "Hey, see that guy?"

"Yeah," Gabriel answered slowly. "You just know he likes it dirty."

Dean rolled his eyes, a habit that became his go-to reaction in regards to Gabriel. Then he realized the kind of statement he had just made and quickly tracked back.

"Gabe. I'm straight and he's a dude," Dean stated dryly.

"Yeah, so what?" Gabriel blinked at him and tilted his head to the side. "Is that a problem? Come on," he screwed his face up in disbelief.

Dean fixed him with a glare. "I'm _straight_."

"Yeah, whatever makes you sleep at night, big boy," Gabriel shook his head and patted Dean's shoulder lightly, "but all I see is you ogling that guy like you want to go all caveman on him."

"Shut up, I'm not-" Dean began, but got interrupted quickly.

"Yes, you are. Look at that ass. Go ahead and tell me you wouldn't tap that," Gabriel smirked smugly. "Well, I definitely would – I mean, the guy even wears a suit," he added with an approving quirk of his eyebrow.

Dean rolled his eyes. "You're no reliable source for an opinion on that. You'd fuck pretty much everything that moves."

"So what? At least I get laid," Gabriel teased and nudged his elbow into Dean's side.

He was not going to answer that, Dean decided. He got laid plenty. Just, maybe, not lately.

And yes, okay, maybe Dean gave in and gave the guy another once-over. He was slenderly built, but apparently sporty with muscles in all the right places. The blue tie he wore was slightly loosened, a tan trench coat hung open around his shoulders, falling open to reveal a classic suit when he lifted his hand to drink from his water. Tax accountant, Dean mused, steady life and income, going to the gym, down-to-earth, reasonable guy. That was about as far as he could describe him from his first impression.

"No way that guy is anything but straight," Dean grumbled, turning away to nurse at his beer.

"Aaah, well, at least you're finally considering," Gabriel waggled his eyebrows.

"Shut up," Dean said again without much force behind his voice. "The guy practically shouts 'I want a wife and house and three kids.' and not-"

"You know what I read some time ago, Dean-o?" Gabriel interrupted his rant. "Guys - and girls, for that matter - who seem pretty uptight at their profession like to give up control at home. In bed, if you catch my drift. Or, in other words, my gaydar says I bet that guy takes it up the ass."

"Even if he does, I don't."

"Does it matter? Only one of you needs to anyway, and-"

"No, Gabe. No, no, no, no, don't you start that again. I know. I don't want to hear about the pleasures of gay sex from you again."

"Might wanna try to ride the gay train for once, Dean. Odds are you might like it."

"For the umteenth time, I'm not into sucking dick."

Gabriel shrugged. "So what if you actually fall in love and the person happens to have a dick attached to them, would you let him go? Love of your life, the one and all that?"

"There's no such thing. Stop playing games with me, alright?"

"I'm not. It might actually happen, you know. Give it a chance."

"One more word, Gabe, and I swear I empty my bottle of beer over your head. Sticky as hell, believe me," Dean threatened, seriously pissed now. To top it all off, the guy walked up to the counter and ordered something from Ellen. Dean swallowed down the lump in his throat.

He had a nice and easy smile, his lips were full and rosy, and his whole appearance was... interesting. He definitely was the kind of guy Dean would like to have a beer and a nice chat with.

"Don't, Dean. You know that's one of the seven deadly sins? Wasting beer, I mean," Gabriel chuckled and took a sip from his own bottle.

"Your face is a deadly sin," Dean growled, and punched Gabriel's shoulder without much force.

Gabriel turned around with a smirk on his face and tapped the guy's shoulder. "Hey, have you met Dean?"

Dean still gaped at him when the guy turned around and big blue eyes landed on Dean, his full lips forming a genuine smile. In the meantime, Gabriel had slipped free and was currently off doing god-knows-what. All Dean could do at this point was stare into that set of intriguing blue eyes.

"Hey," the guy finally said, "Dean, I guess?"

_So we shook hands and had a drink together. He seemed shy at first but opened up pretty quickly. But, like it always is, things just couldn't work out that easily, and I quickly noticed the sour glances he received from his table, where a few girls were waiting for him._

Dean quirked an eyebrow at the group seated in the round booth in the corner before his eyes shifted back to his company. "What's their problem?"

"See the one in the middle, in the black shirt?"

Dean nodded, noticing the weary, bland look in her eyes as she stared into the depths of her wine glass.

"Got dumped by her boyfriend yesterday, so everything that's close to being a man is evil right now."

"Well, that explains a lot," Dean replied and couldn't help but grin. "What makes you so special that they endure your presence, then?"

The man in front of him shrugged, "Hey, I'm just the gay best friend here, so I'm basically harmless." Then he actually winked smugly at Dean.

Not so harmless, then, Dean thought and swallowed. He chuckled then to dub his sudden rush of nervousness, silently cursing Gabriel and his fucking accurate gaydar. The short moment of shock and realization hitting him passed quickly, though. "I see," he looked up into those intense blue eyes then and found himself speechless for a second. Dean swallowed again before adding, "Well, if it helps, you can throw your drink in my face."

The other man grinned. "Still, uhm..."

"Wanna meet up for a beer or two some other time?" Dean interrupted him before he could turn away. Admittedly, he liked him already. He had a nice and easy way to chat.

"Yeah, sure, but I'll be out of town for a week, three days from now. I'm a news reporter, you know."

"Oh," Dean said, making a quick choice at the same moment and reaching out for one of his business cards in his pocket, before he laid it flat on the counter and pushed it over under the other man's hand. He also couldn't fail to notice the neatly manicured hands. Huh. Focus, Dean. "I know it's kind of a long shot, but what about tomorrow?"

Blue eyes shifted up and down Dean's face, searching for something he wasn't sure he would find. A short smile was shot his way. "Sure, I'm free. Dinner?"

"If you like. My number is on that card. It's from the garage I work at, just ask for me," Dean said quickly. "So we can talk about details."

Another short smirk followed. "Will do." Then he reached for his glass of water and threw it in Dean's face, who gasped for air. "Jerk!" He exclaimed loudly and turned around with a wink. Dean was two seconds away from shouting a Bitch for good measure back before he remembered that this wasn't Sam he was talking to.

Then he grinned.

When Dean realized what he had just done – namely, he made an appointment for a date with an openly gay dude. However, he was still straight. In a short moment of panic, Dean's eyes scanned the bar to find Gabriel just about to leave with a hot redhead. Dean waved him over shortly, and Gabriel quickly excused himself to the girl.

"Dude," said Dean.

"What, you got a date?" Gabriel grinned.

Dean eyed him confused. "How did you know?"

"Think I didn't watch you? You look great, I mean, as a couple. Seriously, think about it, Dean. When is the big day?"

Gabriel all but bounced on his feet at this point.

"Tomorrow."

Gabriel pursed his lips tightly. "I thought we were gonna play lasertag tomorrow?"

"How often do I still have to tell you that I will not play lasertag with you?" Dean asked back a bit annoyed, but his smile still in place.

"Fine," Gabriel grumbled. Then he slapped Dean's shoulder apologetically. "Anyway, you got a date. And because I'm your best friend, I don't mind."

"You're not-"

"Bye, Dean-o!" Gabriel interrupted him and took off with the redheaded girl and one last wink at Dean.

"- my best friend," Dean sighed deeply. If he was completely honest to himself, he had no idea what he had just got himself into, and if it would end well. He didn't want to raise false hopes, for that matter, but looking into those deep blue eyes had clearly messed with his head on some level. Another sigh escaped his lips, and Dean tried to focus solely on the fact that it wasn't a date, it was dinner with a guy he just met and could picture as a friend. Get to know each other, is what it was. Or so Dean told himself.

Anyway, Gabriel was out of question to talk to further, and Sammy and Jess probably had sex on the kitchen floor right now. No use going back upstairs. So Dean ordered a glass of good scotch and waited it out, not really interested in conversation of any kind.

Ellen, of course, noticed. "Son, what's got your panties in a twist?"

Dean waved her off, even managing a lopsided smile. "It's nothing."

"Boy, you better not lie to me. You know how that usually ends."

"Me spilling my guts to you and begging for your forgiveness?" Dean smiled genuinely now. Ellen truly was not only a scary potential mother-in-law but also truly like a mother to both Sam and Dean. Seeing as they had lived above her bar for a few months now, she had pretty much adopted the two of them. Of course she naturally picked up on Dean's mood.

Ellen just raised an eyebrow at him then.

"Sorry, Ellen, but I can't quite talk about it now, but it's nothing big, seriously. You can stop worrying," Dean answered as convincing as he could.

"Then you better tell me once you've made up that big head of yours. And stay outta trouble, you hear me?" she added with a frown.

Dean just nodded sincerely. Trouble, yeah, he wasn't so sure if this was trouble. Gabriel's words circled through his mind, again and again. It was just... really, he wasn't gay. The thought alone of going at it with a guy made him shiver acutely.

But then again, looking at the girl at that table over there and imagining her in bed made him shiver just like that. Dean tried desperately not to ponder about it too much until his watch said 11 p. m. and he was pretty sure that he could safely return to the apartment now. After saying his goodbyes to Ellen – and Jo, tentatively and very aware of Ellen's eyes on him – Dean made his way up the stairs and found Sam and Jess already back in bed. Which looked pretty inviting for himself at this point.

So Dean decided to just roll with whatever would come up and went to bed.

_Kids, the next morning and day was crazy. I think I'll better spare you the details, because I'm pretty sure you won't want to hear about it. Let's just say I fuzzed a lot about my hair and clothes and your uncle Sam teased me endlessly about being a girl about this. Which, I assure you, is not something you want to hear when you go on your first date with a guy and already question your manhood. Because that was a date and nothing else, but I didn't realize – or didn't want to realize – it at the time._

When Dean came home that evening, he practically beamed at Sam and Jess.

"Dean!" Jess squealed happily when he closed the door behind him.

"How did it go?" Sam inquired, jumping to his feet and in Dean's way.

Dean couldn't suppress a grin. "Uhm... good, I guess?"

"What does that mean, you guess?" Sam chuckled, but let himself fall back onto the couch and scooted over to make some room for Dean.

"It means... I don't know. I don't know what to think about it, honestly. I mean, he's still a guy, and all, but-" Dean left the sentence unfinished, forming the idea that had just come to his mind and said instead, "Sam, how do I always describe my perfect woman?"

With that, Dean flopped down onto the couch.

Sam's expression became serious when he pondered shortly. "Well, she likes a good scotch-"

"He said he likes, and I quote, 'a scotch that's old enough to order its own scotch.'"

"- she likes olives-"

"He likes olives and I don't," Dean nodded.

"Aw, our olive-theory!" Jess cooed and all three of them grinned.

"- and she wants a house and a dog and one-point-four kids." Sam closed his statement.

"He said he always wanted a husband and a dog. Kids, well, we didn't talk about that," Dean said with a sigh.

"It's probably a gay guy thing," Sam commented, smirking widely.

"Dude, for the thousandth time today: I'm. Not. Gay." Dean rolled his eyes.

"I was talking about him, actually, but... yeah well, if you're already back on your sexuality – I was thinking-" Sam began, but got interrupted quickly.

"I hope you didn't hurt yourself."

"Haha, funny, Dean. Anyway. Who said you have to be gay? I mean, you don't need to think in boxes, okay? You can be bi or just sweet on him or-"

"Dude. Duuuude. Stop right there. I'm not 'sweet' on him," Dean raised his hands defensively.

"Oh yeah?" Sam asked. "Then why don't you tell me how the rest of the date went?"

"Okay," Dean took a deep breath. "We were at that Italian place, you know, two blocks over? Right after we sat down and read the menu, we both noticed that we didn't like the stuff on there. So we went to that small restaurant down that same street and had a beer and a burger and a very good time. I like his sense of humor, he's funny. We stayed for drinks and afterwards, I walked him home."

Sam opened his mouth to say something, but Dean was quicker. "Don't, Sam. It was just because he was living just a few minutes away from here."

"And?" Sam asked after a few moments of silence.

"Nothing. That's it."

"Yeah, what else should have happened?"

"First date, first kiss, anything like that?" Jess helped her fiancé.

Dean hesitated for a second. "What? No!" he eventually replied, his brows furrowed.

"How did you say goodnight?" Sam asked.

Dean shrugged. "Well, he unlocked the door and turned around then and said he had a really good time and offered me his hand. I took it, and said I had enjoyed myself tonight as well, and said good night. I was kind of surprised that he didn't let go immediately-" he left the sentence unfinished, remembering vividly the way he had stood there, the other man so very close to him, holding on to Dean's hand, smiling gently as blue eyes stared into Dean's own.

"Ugh," Sam said, rolling his eyes.

"Dean!" Jess all but flailed her arms in the air. "That was the signal!"

"That was _not_ the signal! There's no such thing as _the signal_!"

"It _was_ the signal!" someone shouted from the kitchen.

"Gabe! What the hell are you doing here?" Dean's head snapped around as he shouted confused in the direction of the room in question. Slowly, Gabriel emerged from it and flopped down on the chair beside their couch.

"Well, I had to know how your date went, right? And would you really have told me everything?" he said with a raised eyebrow, taking a sip from his beer bottle for emphasis.

"Yeah, maybe not," Dean said then. "Still-"

"Still-" Gabriel jumped in. "It was the signal. You could've kissed him."

"He's a _friend_ and I'm _straight_ ," Dean deadpanned.

"What if he was a girl, then?" Jess asked. "Would you have kissed her?"

"No, I mean, the moment wasn't right and-" Dean realized he was in over his head with this.

Gabriel jumped to his feet then, closed the gap to the couch within a split second, and kissed Sam squarely on the mouth. "There, that's what it looks like if someone doesn't give you the signal," he said, while Sam rubbed fiercely at his mouth.

"I swear, I didn't, baby," Sam said towards Jess, who just grinned.

"- but at least I can go to bed tonight and I know: me and Sam? Never gonna happen. You should've kissed him," Gabriel said. "That was probably your only chance and you'll never see him again."

"I can't believe you," Dean replied then, before his eyes fell on the TV which was still running on mute. "Oh."

"What, oh?" Gabriel said, before he followed the line of Dean's eyes to the TV. "Oh."

"What?" Sam and Jess asked in synch as well, confused.

"There he is," Dean explained, pointing at the screen. "He got called to shoot on location the moment I wished him good night. As I said, the moment wasn't right, you just didn't let me finish."

"Wow, he's cute," Jess remarked. Sam just nodded.

Dean couldn't help but smile at the picture on his TV, where the dark-haired, blue-eyed man he had just spent a few pleasant hours with was talking into the camera. Jess quickly reached for the remote and flipped the sound on, and a deep, rumbling voice filled their living room.

" _Oh_ ," said Gabriel.

"He's got one bad-ass voice," Sam grinned.

"Understatement," Dean huffed amused.

Gabriel shot him a sideways glance at that. "I've never heard you say that. It's irritating."

Dean grinned, admittedly a bit embarrassed. "Uhm, maybe I picked it up. He-" Dean pointed at the TV- "-has a habit of saying that."

He was met with Gabriel's rolling laughter. "Oh, you're so precious, Dean. I can't believe you still believe in not being sweet on this guy."

"Am _not_ ," Dean grumbled insistently.

"It still was the signal," Gabriel said. "And you chickened out."

"Did not!"

_I asked him about it years later, and yeah, that was the signal. I could've kissed him._

**The year 2030**

_"And truth is, kids, it actually didn't work out. You know that I don't believe in destiny and the universe and all that crap. But your uncle Sam would probably say at this point: The universe mostly doesn't work the way you want it to. And I might say he's right with that. Because although my life just began to form itself into a bigger puzzle, I didn't realize it at the time. Because this, kids, is the true story of how I met - your uncle Jimmy."_

_"Uncle Jimmy?" - "I thought this was about how you met dad?"_

_"It is, kids, it is. Like I said, it's gonna be a long story."_


	2. Chapter 2

**The year 2030**

_„Okay, so where was I?"_

_„You were telling us how you met dad." - „In excruciating detail."_

_„Right. We sat there on the couch, watching Jimmy's channel-"_

**The year 2005**

"So, what are you gonna do about him?" Sam asked solemnly.

Dean shrugged and quirked an eyebrow at his brother. "Nothing. What should I do?" The question couldn't sound more rhetoric. Also, a bit helpless.

"Well, I dunno-" Sam exaggerated with wide eyes. "Call him? Invite him? I'm not saying you have to hook up with him or anything, but you said you liked him. What's to say against getting to know him? As a friend? Casually?"

Dean scrunched up his nose as he realized that Sam was actually right. "Yeah, uhm... nothing really," he sighed deeply and tried not to meet anyone's gaze but Jimmy's on the TV when he looked up, "But how should I ask him for that and not sound like I want to ask him out? Because honestly, I think he'd be a great friend."

"Weeeell-" Gabriel drew out, his head swinging slowly towards the TV with a meaningful gaze. " _Casually_ , I'd say."

"What? How?" Dean asked back, confused.

"Dude, c'mon. This is not rocket science here. He's a TV reporter. In California. Right where you live. So he has a live show, you know where he is. Be there. Randomly." Gabriel explained, having a hard time rolling his eyes at every second word. "Then ask him. I bet he won't say no."

_Now kids, you know how your dad and I met at a wedding, right? It actually happened because your uncle Jimmy couldn't say No. But more of that later._

A few days later, Dean had just gotten up from bed and was crunching away at his cereal, sitting comfortably wrapped in a blanket on the couch in their living room. The soft click of Sam's door made him look up from the morning news and spot Jessica.

"Morning, Jess!"

"G'mornin', Dean," she mumbled, still half-asleep, and Dean had to grin amused at the picture. That was definitely something she had in common with his younger brother: being a complete zombie in the mornings. Quietly, she padded to the kitchen to set up the coffee machine. That was when Dean almost dropped his spoon and splattered milk all over the place. Almost.

Jimmy was on air. Live from 4th Avenue, which was only two blocks away from their flat.

Dean had never been up from the couch that quickly, slipped into an old pair of jeans and a Led-Zeppelin-shirt and a pair of boots, before running out the door. "Be right back, Jess, just chatting up Jimmy!"

He could imagine her confused face at that pretty well and laughed silently to himself when he jogged down the street. The grocery shop Jimmy had just reported from wasn't very crowded, and it was easy for Dean to slip in and avoid the camera until their footage was shot. He hadn't even noticed what the report was about.

He proceeded to grab a six-pack of beer because he didn't find anything else to busy his hands with, when Jimmy turned around and noticed him. Dean stopped in his tracks, suddenly shell-shocked and rooted to the ground, as if they truly had met randomly. "Hey, Dean! What're you doing here?"

"Oh, I'm just, uh... grocery shopping," Dean answered, presenting the six-pack to Jimmy, "you know, because, we're... throwing a party. Wanna stop by?" he burst out in a hurry.

Sam was gonna kill him. The guy had a paper to write until Monday, and as far as Dean had noticed during the past few days, he was more occupied with having sex with Jess than working on said paper. Well, she was... persuasive. And extra-affectionate since the day Sam had put that rock on her finger.

_"Ew, dad!" - "Yeah, I know. Just for the record. Women can be that way, son. Men too." - "Daad!" - "So, anyway-"_

"Yeah, would love to. When?" Jimmy asked, a glance in his eyes that acutely made Dean's stomach curl with something strange. He didn't really want to think about it.

 _Please don't assume too much,_ Dean silently prayed to whomever-is-up-there, saying "Tonight. You free?"

"Sure, I'll be there."

With that promise, Dean went home and couldn't help but feel quite giddy. He had picked up a few supplies for the party, plenty of beer and just hoped that Sam wouldn't scratch his eyes out. Dean's, of course. Damn, he needed to get his act together.

When Dean returned to the apartment, he found Sam and Jess having breakfast on the couch, still clad in their pajamas – or morning robe, respectively. "So?" Jess asked with a wide smile.

"Guys, better get dressed. We're gonna have a party tonight." Dean announced, pretending excitement. Truth was, he was too unsure where he wanted to go with this to be fully happy about the evolution of... things. "Sorry," he added quickly towards his brother.

"Wait, what?" Sam asked grimly. "You know I've got a 25 page paper on the history of domestic relations law between 1850 and 1900 to write. Right?"

"Yes?" Dean offered with an apologizing smirk. "C'mon, Sammy."

Sam rolled his eyes in defeat. "Okay. But I swear, you own me for this. Jerk."

"Bitch," Dean replied easily and began to clean the kitchen.

The rest of the day was spent with setting everything up for the party and by 9 p. m., the apartment was full of people, standing and sitting all around the living room with beers in their hands. The atmosphere was easy and bustling and allover comfortable. Everyone was there, even Gabriel – chatting up a guy in low-cut black jeans right now with his charm full-on – but Jimmy hadn't shown up so far.

Dean was not amused, to say the least. Even if he was also kind of worried and relieved. And schizophrenic, apparently.

Anyway, Dean did what he did best: he panicked. "Sam! Hey, Sam," he grabbed his brother's sleeve and pulled him into the kitchen. "God, what did I think?" Dean asked, more to himself than to Sam, who snickered.

"Dude, since when do you ever think before you speak?" he laughed, then punched Dean's shoulder lightly. "Seriously though, what's up?"

Dean rolled his eyes. "What should I do when Jimmy shows up? I have no clue!"

"You're gonna offer him a beer and make some smalltalk, and then you go up to the roof with him."

"Why the hell would I go up to the roof with him?"

Sam raised an eyebrow. "Uhm, because the roof is amazing at night and I don't know any better sure-fire way to light the romantic spark between you two? If there is one, of course."

Dean groaned.

"No, Dean, before you say something: just try to not screw this up, okay?"

"Why will no one believe I'm straight. Christ. I need new friends," Dean mumbled exasperated, rubbing his temples absent-mindedly. "I think the guy harbors too much hope for... this-" at a lack of a proper word to describe his current situation with Jimmy, Dean helplessly flailed his arms in the air, "already, I don't want to raise even more false hopes. That's not fair. And what if he doesn't even show up today?"

"He will show up," Sam said, nursing at his beer.

_He didn't show up._

"How big do you want your 'I told you so' to be, Sammy?" Dean asked the next morning when Sam stumbled lazily out of the bedroom in the early afternoon. Jess followed him with puffy red eyes and yawning all the way to the kitchen.

"'s okay, Dean," Sam shrugged. "I'm cursed enough by the fact that I haven't even started on my paper yet, you know. Two days before its due date. Do we have coffee?"

"Jup, 'elp yo'self," Dean answered with his mouth full of cereal as he switched the TV on.

Jimmy, of course, grinned back at him.

Dean quickly changed the channel.

After breakfast and cleaning up the mess that was left of last night's party, Dean had to leave to run some errands – and really, when he ran into Jimmy this time, it was truly accidentally.

"Dean!" Jimmy waved. "Hey! Dude, I'm so sorry for not stopping by yesterday, I got caught up at work."

"Nah, don't worry," Dean answered, slapping him lightly on the shoulder. What followed was a luckily short moment of awkward silence. None of them really knew what to say, both instead staring down and toeing the tiles on the floor.

"I wish your party had been tonight, you know. I don't have to work today," Jimmy eventually said meekly and with a small smile.

And before he could stop himself – yeah, the whole talking-before-thinking-issue once again – Dean burst out: "Hey, you know what? There actually is another party tonight. So stop by, if you want."

Jimmy seemed puzzled for a moment, but eventually answered cheerfully, "Thanks, I will! Promise."

They even shook hands to seal the deal.

When Dean came home and gingerly broke the news to Sam and Jess – who just left the bedroom once again, subtlety be damned – Sam eyed him with the best bitchface he could manage while only wearing his boxers, pants still laying around somewhere on the bedroom floor. "Seriously? And my paper... oh never mind," he grumbled. And packed away his books and laptop.

And luckily for them, Sam had a lot of college friends who had no problem with partying two days straight. The apartment was filled to the brim with guests once more when Dean found himself standing in the kitchen and fidgeting with the label of his beer bottle. "He won't come, and I'm not sure if I should be happy or not," he muttered into his non-existent beard.

"He'll come," Jess said. "Why would you be happy if you wouldn't see him?"

Dean shook his head. "This whole thing, whatever it is, is just crazy, Jess. I mean, this is the second party we're throwing just to get to know him-"

"Yes, and so what? Even if you're right, and there's nothing there, what makes you think he won't be a good friend anyway?" she gently placed her hand on his shoulder and kneaded it softly. "C'mon. I know you're not good with the whole feelings-crap and all that, but nothing's wrong with getting to know people. I'm not saying anything here besides: give him a chance. Dean, all you do is hang out with your brother. And his girlfriend."

"And Gabriel," Dean added, but realized quickly that this fact wasn't really speaking for himself.

"And Gabriel," Jess nodded and rolled her eyes. Then she smiled at him.

Dean smiled with understanding before he was caught in a short, encouraging hug by Jess. He huffed. "What did my brother do to deserve you, huh?"

Jess still smiled when she pulled back, then went to the fridge and handed Dean another beer. "There. And play nice, you got me?"

"He won't come anyway," Dean said sheepishly.

"Who won't come?" a strangely familiar voice asked, and a dark-haired head emerged from the door frame to the kitchen.

"Jimmy!" Dean said, almost spitting his beer all over the Johnny-come-lately.

"The one and only," Jimmy grinned. They shook hands shortly – like men, with a short slap to the shoulder.

"You want a beer?" Dean asked, opening the fridge.

"Yeah, sure," Jimmy answered. His voice sounded much lighter than when he played the serious TV reporter, Dean noticed. He also kind of liked the deep, rolling voice a lot more, he stated to himself. Why the hell did he think such things anyway? Focus, Dean.

They clinked their bottles in a silent toast and both took a swig of beer.

"So, how was yesterday's party?"

Dean shrugged. "It was okay, nothing special. We had fun and-"

"Hey," Sam's voice shouting from the living room suddenly interrupted Dean. "Has someone seen my issue of Domestic Family Law in the United States from 1750 to 1950?"

Everybody just looked at Sam with big, innocent eyes.

"Has anyone seen a big-ass book?" he added exhausted.

The answer was a collective, indifferent shrug.

"Oh, never mind, I've just got a paper to write and- Oh no. Are you fucking kidding me?" Sam suddenly said in shock, peeling a crust of chips and mini pretzels and coke off said big-ass book, which had apparently served as a tray during their parties. He was pissed, to say the least, and displaying the best Sam Winchester(tm) bitchface.

"C'mon, let's get out of his line of fire," Dean mumbled quickly and waved Jimmy over to the fire exit.

"Where are we going?"

"The roof."

"Why are we going to the roof?" Jimmy asked confused.

"You'll see," Dean smiled mischievously.

When they had climbed the fire escape ladder and stood on top of the building, it became abundantly clear. The stars were shining bright that night, with no cloud obliterating the Californian night sky. The moon was cutting out the remarkable skyline of Palo Alto, and the lights of San Francisco could be spotted in the distance. It was beautiful and quiet and quite romantic, even Dean had to admit that.

Dean sighed. "Needless to say, the view from here is _beautiful._ "

Jimmy huffed, "Understatement." and Dean had to laugh at the trademark answer of the other man. The laughter resolved to a quiet, wide smile when Jimmy put his beer on the edge of the railing and turned to Dean, fixing him with his deep blue eyes that shone in the moonlight.

It was so romantic that Dean could puke. He didn't, though, because in that very moment, he wasn't even able to think about it, didn't care if this was a chick-flick moment. Because there was Jimmy, his stunning blue eyes and full rosy lips, right there for him to take – and Dean still wasn't sure what he should do about him.

 _Well, do him, dumbass!_ the tiny Gabriel with little wings and Devil's horns on his shoulder deadpanned. Dean did his best to ignore him.

"Did you bring me up here for the reason I think you did?" Jimmy asked quietly, eyeing Dean cautiously. Damn this guy and his stupidly sexy deep voice that he could alter so easily.

"Honestly? I dunno, Jimmy," Dean said with a sigh, avoiding his gaze and instead staring into the moon. No, he didn't want to pretend. And he didn't want to lie.

"What is it you don't know?" Jimmy asked softly and confused.

Dean just huffed. "What this is."

Jimmy quickly interrupted him. "Why do you feel the need to worry about it so much?" he smiled, watching Dean quietly with an amused sparkle in his eyes. "So I'm taking a wild guess here, but apparently you're feeling it too?"

"Feel what?"

"That there might something be there. Between us."

Dean shrugged, at a loss for a proper solution. "Listen, I want to be honest with you - I'm not really into guys. I mean I haven't been ever before and I don't know how this could or should work. And I don't want to promise anything I'm not sure I can give," he answered solemnly and took a deep breath before he looked into Jimmy's eyes again. "I just don't want to raise false hopes."

"Dean... I understand that you have doubts. Just try to shut them off for a second and we try something, okay?" Jimmy smiled softly and shifted closer, laid his hand on Dean's shoulder. He watched Dean closely, waiting for the approving nod before he slowly trailed his fingers over Dean's collarbone until he eventually wrapped it around Dean's neck. They practically breathed the same air at this point, and Dean could feel the heat radiating from Jimmy's body as blue eyes locked with his. He was given all the time he needed to push Jimmy back, but he didn't. Truth of the matter was, Dean wanted to try this, and thank god for Jimmy's courage, because Dean would've never suggested it. But he was curious.

At this point, it were mere inches that separated their mouths, so Dean made a fast decision. Closing the gap between them, Dean shut his eyes and pressed his lips to Jimmy's, kissing him tentatively. After a short gasp for air, Jimmy reciprocated it with a gentle nip to Dean's bottom lip, letting Dean take control of the movement by tilting his head to the side.

The first thought that hit Dean was that it didn't feel much different from kissing a woman. Lips were lips, physically speaking. Only the stubble grazing against his cheek when Jimmy moved was new, but barely more than a bit distracting. The kiss turned languid and slow then, trying and tasting and teasing. After a few moments, they broke the contact to gasp for air. Dean leaned his forehead against the other man's and breathed in deeply. So that was his first gay kiss. Not so bad, indeed, but-

No, he didn't feel the spark everyone was talking about. Sure, he was nervous, but not in that butterfly-in-his-stomach kind of way. Sure, Jimmy was a good kisser, but his kisses didn't make Dean's body react in the way he expected it to do. And sure, Dean could apparently enjoy a kiss with another man. It still didn't mean he wanted to jump Jimmy's bones.

Dean shoved Jimmy away softly, realizing at the same time that his hands were placed on Jimmy's hips. After dropping them, he said silently, "Jimmy, listen... I don't think this works."

"I know," Jimmy replied with a sad smile.

"You know?"

"Felt it in the kiss. If there's nothing there to work with, then there's no hope that a relationship would work. Although I have to admit that I kind of hoped there was. And that I could make you see that if I kissed you," Jimmy explained, cupping Dean's cheek in his hand while still smiling ruefully.

"Well, don't get me wrong, the kiss wasn't exactly bad and... God, I think I'm gay," Dean groaned and covered his eyes with his hand. "Or bi or something."

Jimmy grinned. "So at least I helped you see that."

Dean couldn't suppress the smile that tugged at the edges of his lips and dropped his hand. "Yeah, I suppose. Still, I'm sorry, and you're a really cool guy. I know it's a lame attempt and all, but do you wanna hang out some time? As a friend? _Casually_?" Dean emphasized that last word with a nonchalant wave of his hand and a shrug.

Jimmy nodded with a gentle smile.

When they went back to the apartment after that, most of the guests had left. They didn't spend that much time on the roof, did they? Dean quickly searched for Sam, who was about to do the dishes with Jess. "Where the hell did all the people go?"

"Oh, after Sammy's raging fit they remembered there was that really cool party downtown they just had to stop by tonight," Jess answered with a wink.

"Well, then I think I'll better get going as well," Jimmy said quickly.

"Wanna come over tomorrow? To hang out at the bar?" Dean asked him with a lopsided smile.

Jimmy nodded and hugged him as a matter of goodbye, and Dean helped his roommates to clean the apartment.

The day after that, on Sunday, Sam and Jess sat beside each other in their usual booth in Ellen's bar, with Gabriel lounging at the short side of the table, a glass of scotch in his hands. Dean made a beeline for it and flopped down opposite Sam.

"So, Dean-o," Gabriel addressed him after a dramatic slug of his whiskey, "Care to explain why you didn't fuck your significant other's brain out yesterday?"

"Because he's not my 'significant other', midget?" Dean shot back without much venom in his voice.

"Classy, Dean. At least I don't have to overcompensate."

Dean gave him an overly sweet smile and said nothing, not really in the mood to pick a fight or bicker.

"Dean," Sam started, "as your brother and your best friend-"

"I thought I was his best friend!" Gabriel interrupted them, but was ignored by both Winchesters.

"- I have to say, I'm proud of you for giving it a shot and being honest with him."

Dean rolled his eyes. "You done? Jess, don't let him watch any more of your rom-com flicks, okay?"

They all grinned at each other, knowing that Jess surely didn't watch anything like those chick-flicks that Dean dreaded. Her favorite movie was Star Wars. Then again, how the hell had Sam managed to score a girl like her? Yeah, right. Nerds. Both of them. The couple just exchanged a short kiss when another voice sounded from behind Gabriel.

"Hey guys," Jimmy said with an awkward wave, wearing his usual trench coat.

"Hey Jimmy," Dean greeted him, smiling and nodding at the empty seat beside him. "Meet my brother Sam and his girlfriend Jessica. The douchebag over there is Gabriel. Don't listen to him under any circumstances."

After a handshake with everyone, Jimmy sat down and made some small talk. Dean couldn't help but watch him, eyes fixed on his lips, and still remembered their kiss yesterday vividly. And he was glad that he could go to bed that night, knowing him and Jimmy? Never gonna happen.

He still couldn't nail down that strange feeling in his stomach.

The most important part, however, was that Jimmy and the others got along just fine. Which Dean was definitely glad for.

"I'll get us a couple beers," Jimmy said right then, rising to his feet to head for the counter.

"I'll come with you," Dean added quickly and followed him.

When they both reached the bar and Ellen already uncapped a few bottles for them, Jimmy turned towards Dean. "So, we're good?"

Dean nodded. "Totally," he said and smiled.

Jimmy returned it genuinely. "Good. Because you, my friend – and don't lie to me about it – really are in need of a boyfriend or girlfriend. And I will help you to find the right one."

Somewhere between the 'What' and 'Why' and 'Are you crazy' that lay on the tip of Dean's tongue, he heard Jimmy say, "Hey, have you met Dean?" and subsequently turning around with a wink. And the beers in hand, leaving only one for Dean.

Still busy snapping back to the present situation, Dean looked at the guy Jimmy had chatted up. But truth be told, Dean wasn't up for a conversation with a stranger and found himself repeatedly looking at their booth, with Jimmy and the others talking and laughing. His eyes were mostly drawn to Jimmy, though. Dean blamed it on those damn blue eyes. After a few minutes, he excused himself from the guy whose name he didn't even get, much less his number, and returned to their table.

"Sam, any plan on what to do with your paper?" Gabriel just said when Dean slipped into the booth.

"You know what?" Sam answered, grinning at the shorter man. "Imma knock back that beer, then knock back another one, then I'll go up there, write my 25 pages on Domestic Family Law between 1850 and 1900 and Imma get an A. Suckers."

_He did get a B+. Still, 25 pages in one night? The kid was good._


	3. Chapter 3

**The year 2030**

_You know, kids, if I had met your dad at this point in the story, I would probably have had a freak-out or a mental break-down or something in between. What I'm saying is, I wasn't ready. Realizing your true sexuality when you're almost thirty, that's one thing. Deal with it is the other. And I was so not ready for all this. But let's not skip anything important here._

**The year 2005**

"So you're, what, bi now?" Sam asked, raising an eyebrow at Dean. He seemed tired as hell, just returned from law school after bringing in his paper that he had spent the whole night on writing.

"I guess," Dean who sat beside him on the sofa shrugged as an answer. "It doesn't feel like much of a stretch, though. I mean, yeah, Jimmy is hot and all that, but we just didn't click on a higher level, if you know what I mean. It wouldn't have been much different if he was a woman."

Sam nodded in understanding and yawned.

"I didn't change that much, I just..." he added, noticing that stating it so bluntly made him feel a bit strange, "Dunno, opened the circle of possible lays to the other half of the population? Which really isn't a bad thing, just saying." Dean tried to look smug.

"I know, Dean. And I hope you know you've got my full support in this," Sam said solemnly. "You are my brother and I won't love you any less because you're bisexual."

"You know, I'm the one who just admitted to being into dick and you still sound like the gayer one of us."

"Shut up," Sam replied with a soft smile and punched Dean's shoulder. "I'm the one who's getting married to a woman in four months, so suck it. Literally. And with that, I'll go to bed now."

It was 8 a. m. when he said this.

Dean went to work after that, and thought everything was going to be the way it always was. Except that he was strangely aware of every man and woman he passed by on the street. For the first time in all his life, Dean paid attention to the guys as well, which felt weird. There were no boobs to make a first impression, hairstyles were mostly mundane, and if he looked closer to judge a man by his features and built body, well, then that really seemed outwardly gay. Dean wasn't sure if he was ready for that. Then there was the fact that he couldn't chat up a guy like he would a girl, even if he wanted and dared to. Obviously, a not so small part of them would rather be offended by a man hitting on them.

Still, that guy walking into Singer's garage that day, clad in a tightly fitting black suit, white shirt and red striped tie was pretty hot. And as straight as they come, unfortunately.

Good thing was that Dean was half-hiding with his head stuck in the engine of a car hoisted up on the service lift. At least he could check out the guy's ass like this.

Seriously, how did gay guys manage to get laid?

Sure, Dean was new to this, but suddenly, there were thoughts piling up in his head that he quietly stored away for later. Maybe he'd find time to call or meet up with Jimmy later today or tomorrow.

What he understood from day one, was that being bi didn't really make anything easier in his life.

Dean knew he was still at the beginning. That he only recently accepted that he was drawn to men as well as he was to women – and that it was okay. That kissing a man really wasn't that bad, rather the opposite. But having sex with another man was something different. Dean shuddered involuntarily at the thought.

He told Gabe as much that evening in the bar. The bastard just laughed at him.

"Dude, the moment you meet the future Mr. Winchester, you'll see. You'll want to bang his brains out, no matter how or... you know, just not overthink it."

Jimmy chose that moment to flop down beside Dean, three bottles of beer in his hands. He quickly handed Gabriel and Dean one each before raising an eyebrow. "What are we talking about?"

"How to get gay sex 101," Gabriel grinned.

"Oh," Jimmy said. "Well... what do you think of going out this Friday? There's a pretty cool disco down town."

Dean screwed up his face in disgust.

Jimmy noticed it immediately. "Don't get me wrong. It's that kind of disco."

Dean was still skeptical.

Gabriel waggled his eyebrows suggestively. "C'mon."

_Kids, your uncle Gabriel sometimes has the most fantastic, awesome ideas ever. Unfortunately, for every great idea he has, there are at least ten horrible ones. This one was of the last kind. So this is the story of how I ended up in a gay disco for the first time._

The atmosphere was strange and unsettling.

 _Understatement_ , Dean thought and sighed to himself. Well, at least there was a bar. The beer he got handed there was, unfortunately, not even a regular glass, but some smaller, fancy bottle. Huh. It didn't taste half bad, though.

The thing about this... establishment though, that had Dean squinting and staring into the floor, were the guys around him. Sure, there were a few pretty good-looking guys running around here, but they either had two guys left and right hanging from their arms or they were dancing. And really, the dancing, the music they were dancing to, it was ridiculous.

Dean just wasn't into techno pop music at all.

Not even hot, shirtless guys gyrating their hips to the beat could save his evening.

Plus, he felt ridiculous in his usual jeans, plaid shirt and black shirt underneath.

Gabriel, of course, had a ton of fun. He had jumped on the dance floor the moment they had entered the disco, and apparently liked groping random guys, not caring that most of them were at least a foot taller than him. And right when Dean decided to get drunk and suffer through this no matter what, the short brunette man hopped off the dancing stage with a hunk on his hand. It was too loud to talk in the room, so Gabriel just smirked and nodded towards the backrooms.

Which Dean hadn't even noticed before.

_And no, kids, I won't tell you what was going on there. That information is very much classified NC-17._

Dean rolled his eyes and turned to Jimmy, who wore a pained look on his face and immediately clinked bottles and gulped down his beer at once. Dean grinned at that, which Jimmy reciprocated through a cough.

On some kind of mutual agreement, they ordered a shot of whiskey each. The night got presumably better after that. After an hour, Dean felt pleasantly buzzed and didn't so much as protest when a rather good-looking blonde with a gray t-shirt that was cut so low it hardly covered his nipples pulled him up unto one of the dancing platforms. Dean couldn't dance, of course not, but he was intoxicated enough to try.

_Kids, there are things you will never see, no matter how much you beg, and me dancing with your Uncle Balthazar is pretty much the first item on that list._

Through the alcohol-induced haze, Dean noticed about three songs in that this really wasn't his style. The music, the dancing – not even the guys, mostly. He wasn't into those hunks that towered over him, and god knows what they took to make those muscles bulge like that. Dean didn't find it sexy in the least. Then there were the younger guys, barely grown-ups, with blond, floppy hair and slender bodies – no, really, no. Dean wasn't into _boys_ either.

He wanted a man, for crying out loud. A simple, average guy. Not a body builder or a wrestler or a twink.

Dark hair came to mind then, and big blue eyes.

At this point, Dean excused himself to the man he would only later get to know better, and stepped off the dancing platform.

Jimmy leaned idly against the bar, another whiskey in his hands. He smiled meekly at Dean before his eyes snapped to something behind Dean's shoulder. When Dean spun around, he found the blonde man he had danced with, and a question was shouted into his ear. He didn't understand shit, it was too loud. So Dean just pointed at Jimmy and shook his head apologetically. The man looked confused.

So Dean did the only thing that he could think of. He walked straight up to Jimmy and after shooting him an 'it's okay'-look, cupped his cheek with his hand and kissed him on the lips. Not just a peck, but a short kiss.

"He's gone," Jimmy said afterwards, yelling into Dean's ear, but he could still barely hear him.

"I'll be deaf tomorrow!" Dean shouted back, but Jimmy only shrugged. Obviously, he couldn't hear anything himself.

On an impromptu idea, Jimmy shoved his glass of scotch into Dean's hand and motioned for him to drain it. So Dean did. Then he put the glass back on the counter with a loud bang. Jimmy grinned, took Dean's hand and pulled him outside.

"Dude," Jimmy said, his voice already sounding hoarse, "I'm not sure if I want to repeat that experience."

"Yeah, me neither," Dean coughed.

"You think Gabe's gonna be fine in there?"

"Sure. He's Gabe," Dean winked. "Anyway, I want a quieter place next time."

Jimmy looked up into the star-lit sky and pondered. "I think I know one," he said.

"Okay, then. Is it far? Or would you rather go home?"

"No, it's really not far. Wait-" Jimmy left the sentence unfinished as he waved down a cab.

And so, they ended up a few blocks away, in a small bar that played classic rock music – Dean approved – had good beer in pints – Dean approved – and a rainbow flag hanging on the wall behind the counter. Dean liked it. Not quite like Ellen's, but still.

Conversation flowed nice and easy between him and Jimmy.

_The bar was cool, the guys there were cool, and seeing this, I was pretty damn cool with being bi. So if you wonder why I wasn't ready to meet your father at this point, it all comes down to New Year's eve 2005._

_Kids, when you are halfway to reach your 30th birthday and your baby brother is about to get married, you start to think. Compare your life, see what you achieved over those past years. Eventually, you'll think about all the things you did wrong, and I surely got plenty of that on my list._

_Jo is one of them._

_Truth is, when you start to get insecure and don't want to admit that to yourself, you start to get stupid. Or so I heard. Because you know, your Aunt Jo is great and all, but… I'd rather start the story from the beginning._

**New year's eve 2005**

"Dean, please tell me you bought some fireworks," Sam growled, sounding panicked.

Dean huffed. "Please. How could I forget the firewo-"

A loud pang interrupted him right then and caused the brothers to search around the apartment, only to spot Gabriel at the box Dean had stored the fireworks in.

"Oops… uhm, found 'em?" Gabriel shrugged apologetically and was only met with nonplussed gazes from Sam and Dean.

Dean immediately jumped over and held his hand, palm upwards, towards Gabriel. "Gabe, any lighter you have. Now," he snarled.

"I'm not a kid, you know," Gabriel replied and rolled his eyes, before he reached into his pocket to hand Dean a blue lighter.

"I said all of them," Dean deadpanned, raising his eyes suspiciously.

Gabriel stared. Dean stared right back. After what seemed like forever, Gabriel sighed in defeat and put a box of matches alongside the lighter. "But promise to give them back!"

"Yeah, at midnight," Dean grunted and placed both items on top of the Gabriel-proof kitchen cabinet. Gabriel-proof because the cabinet was too high for Gabriel to reach, and it would have definitely have caught Dean's eye if he would have taken a chair to the kitchen. "And stay away from the box, are we clear? No lighting fireworks indoors."

Gabriel just grumbled some more.

"Don't make me call in a last-minute intervention about your pyromania."

"Fine," Gabe snarled and took off, leaving them to prepare the flat for the New Year's party.

"Hey, we didn't have an intervention for a while now," Sam mused out loud, but grinned widely.

"Yes, because the last one went so well," Dean chuckled and headed off towards the kitchen to put some beers into the fridge. He didn't even bother to place them separately in, just shoved six-pack after six-pack into the fridge.

Jess raised an eyebrow at him, apron still wrapped around her waist from frying some patties for the burgers earlier. "Uhm, Dean… do you want to put the salad in between the bottles or what? Like, leaf by leaf?"

Dean blinked. "Oh," he eventually answered intelligently and replaced one six-pack with the salad bowl Jess handed him with a bright grin.

When the door bell rang, Sam jumped to his feet. "I'll get it!"

"Dude, do we ever get a fucking break today?" Dean sighed loudly, before he was interrupted by two arms coming up and locking around his waist, squeezing him tight.

"Hey, Dean!" Jimmy greeted him, his mouth right behind Dean's ear.

If Dean shuddered just a bit, he quickly dubbed it with a breathy "Geez, Jimmy! Need Air! Now!". Jimmy pressed him close one more time before letting go. Dean gasped for a short second and turned around to whack him on the shoulder.

"Ouch!"

"Deserved it, sucker," Dean snorted without much venom in his voice. He also couldn't help but grin at Jimmy's pouty face afterwards. And he should definitely not watch those lips too long, because damn they were distracting.

Problem was, Dean knew he didn't want Jimmy, not in that kind of way, but still was very aware of the physical attraction to him.

"Anyway, guess whom I met downstairs?" the man with the stunning blue eyes asked while grinning back at Dean.

"Dunno, shoot," Dean shrugged.

"Jo," Jimmy answered. "She said she would have to help Ellen out at the bar today, so I invited her over to your flat afterwards. Hope that's okay? She said all of her friends were at some other guy's party and she didn't really intend to go on any New Year's party. And I mean, that sucks."

Dean startled for a moment. Yeah, Jo. Jo was sweet, and cute, and awesome. And Ellen's daughter. But...

**Ten hours later**

Dean was drunk. No, scratch that. Plastered. Yeah, well, it was New Year's Eve. He was allowed to be plastered.

So he grinned widely when Jo joined them on the roof at midnight. They were all shivering in the cold, intending to watch the fireworks at midnight.

Anyway, Jo made a beeline for him and that just made Dean really excited.

"Hey, you made it!" he said, greeting Jo with a hug.

"Yes, mom said I could go up to you if I would be back down in twenty minutes," she grinned right back.

Dean wordlessly handed her a beer. His eyes were fixed on hers as their fingers brushed, and okay, maybe he was plastered and then some.

Which was also clearly the one and only excuse when he – merely five seconds later, when the first fireworks exploded over their heads – leaned down and kissed her. She hesitated for all of a short moment before kissing Dean back, and what started out as an innocent brush of lips quickly turned into something more urgently.

Damn, Jo was hot, and that was also the way she kissed.

_Dad, TMI. - Sorry, son. What I'm about to say is much more important, though. Don't overestimate yourself when you're drunk. Or don't get drunk at all, that is. And don't kiss someone you like just because you're drunk._

Dean broke the kiss after a few seconds to stare at Jo. Brushing a strand of long, blonde hair back behind her ear, Dean stated to himself that yes, being bisexual was awesome, because he was still allowed to have this and like it. With a wide grin, he wrapped Jo up in his arms and kissed her passionately.

Gabe wolf-whistled at them from a few feet away. Dean flipped him off without even breaking the kiss.

About ten minutes later, Jo left with the biggest grin on her face and promised to show up again when she was done at the bar.

The only thing Dean remembered after that is Tequila shots, a blurry, spinning world, and at some point, his bed.

When he woke up the next morning, long blonde hair was draped all over his chest. Dean shifted awkwardly, which made the blonde bundle in his arms sigh displeased and reminding him of the headache threatening to split his brain in two and the sickness welling up in his stomach. It took him quite some time to recollect his senses and memory of the past night to figure out it was Jo laying in his bed.

Another tentative shifting made him very aware of the fact that they were both naked. It also made him gasp surprised in a very embarrassing way, which effectively woke Jo up.

"Dean?" she mumbled from somewhere on his chest.

"Yeah?" he croaked, his voice breaking. "Did we-"

She was up in about two seconds flat. "You say you don't remember anything? All the things you said? What we did?" she asked in a high-pitched voice.

"Uhm..." Dean swallowed heavily. "No?"

"I can't believe it. I mean, I know you were buzzed, but... shit." With that, she collected her clothes and hurriedly put them on. "Forget it, okay? The part that you still remember, of course. Jerk."

And with that, she was out of the door and gone.

Dean grunted in frustration, fell back into the sheets and decided to go back to sleep. Right before his eyes fell shut, he noticed two things: a condom carelessly thrown on the floor beside the bed – which, ew, even for him – and a pineapple standing on his bedside table.

Hours later, Sam woke Dean up with a loud "Thank you very much, Dean, now we can't go down to the bar for at least a few weeks!" which was immediately followed by Gabriel, jumping into Dean's bed, pulling the blanket away from him and shouting "You do not ruin the bar! That's our ground rule number one! No ruining the bar, asshole!"

Dean got a few pillows slapped against the head, right before Sam said. "Oh, this is where the pineapple went."

"Where did it even come fro-" Dean was interrupted by the pillow thrown into his face once more by Gabriel.

"I don't know, you picked it up somewhere last night and wouldn't let it go, not even when you stuck your tongue down Jo's throat."

Dean moaned and grabbed the pillow out of Gabriel's hand, just to cover his face with it.

"Gimme that, vitamins are the best cure for hangover anyway," he heard Sam say amused, his voice muffled through the pillow.

Gabriel left him alone as soon as he noticed that Dean wouldn't respond to his teasing and punching – sans the pillow now – at all.

Dean went back to sleep, and decided quietly to swear off both men and women plus alcohol for some time. He had made that promise to himself without asking the universe, though.

**The year 2030**

_They told me later that it was all a charade, that they were only messing with me. I never slept with your Aunt Jo, I was way too drunk for that. And Sam and Gabe just loved to play pranks, especially on me. Jo had already figured out that we wouldn't fit for each other – apparently I had been drunk rambling about Jimmy's blue eyes a bit too much. Which was also the reason why Ellen did not throw us out of the bar when we – undaunted by death – went down there the next time. Jo had never told her what happened._

_In hindsight, this was probably the last time I tried to prove myself that part of me is still into women, that I also could have some normalcy in my life. But you never know. And when I decided to take a break from dating and sleeping around to get my head clear, the universe sent me a sign. At least that's what your uncle Sam calls it._

_The first time I heard of your father, it was Sam who talked about him. "Hey, Dean, the wedding planner is taking us to the pastry shop tomorrow, so we can meet the confectioner and choose our cake."_


	4. Chapter 4

**The year 2030**

_So we went to the confectioner the next day to have a look at the cakes. I, of course, tagged along. You know your dad, kids, I can't resist when pie is involved. Or cake, for that matter._

_And you know that I always say I met your dad at a wedding, right? Well, it's not entirely true. We knew each other before that._

**The year 2006**

The bell above the door chimed when Sam and Jess stepped through hand-in-hand. Dean walked a few feet behind them, checking the scene carefully.

"Hi," Sam said. "Uhm... we're the 11 o'clock appointment?"

The pastry chef grinned at them and took a few steps around the counter to stand before the couple. "Welcome," he said. "I'm glad you found your way over. Please follow me, I prepared a few cakes for you to try. The wedding planner informed me of your preferences, so I hope there's something you like there."

Dean could just blink and stare after him. Dark, tousled hair, stubble, and a nice smile. Huh. Interesting.

Sam interrupted his train of thought by elbowing him into the side. "Hey Dean," he stage-whispered. "Three o'clock."

Looking into the direction he was told, Dean noticed a set of little wedding couples made of marzipan. The little figures you put on top of the wedding cake. As it turned out, there were not only bride and groom standing there, but also couples that consisted of two grooms or two brides. When he looked back at Sam with a questioning look, Sam just waggled his eyebrows suggestively. Then he smiled at Jess as she pulled him to the back room.

Dean rolled his eyes and followed.

The cake-tasting itself was not that eventful. Sure, every single one of the pastries was really good – but who was he kidding, it just wasn't pie. Dean mostly spent his time watching the pastry chef anyway. He was kind of cute, and he couldn't stop his eyes from looking at him every two seconds. The chef, on the other hand, quickly noticed his glances and shot Dean a wide smile.

Oh.

Dean had to swallow at this point, had to consciously refocus on the cake.

Luckily, Sam and Jess quickly decided to have the lemon and walnut cake which Dean also found pretty enjoyable. When Sam paid and they left, he shared another glance with the cute pastry chef – only to have a piece of paper shoved into his palm when they shook hands as a matter of goodbye.

Unfolding it the second they were far enough away from the shop, Dean found a phone number scribbled on it, complete with a note saying "Call me! Andy".

"Aw," Sam cooed, looking over Dean's shoulder.

Dean punched him good-naturedly. "Shut up."

Sam snickered then, grinning widely. "Well, our wedding planner already said he could be like that. When I said my brother was bi, he suggested to take you with me so you would have a little fun, too."

"The hell? That are the kind of things you discuss with your _wedding planner_?" Dean eyed him in disbelief, but Sam just shrugged. "And anyway, since when can you even afford a wedding planner?"

Sam's lips twitched into another grin. "He's a... friend of Jimmy's. Jimmy might have given us his name and address and put in a good word for us?"

Dean shook his head. "Whatever."

"You should come and meet him some time. He's awesome."

Stopping in his tracks, Dean felt heat flare up within himself, and not the good kind of it. He waited until Sam turned around to him to glare at him and snap, "Thanks for your support, Sammy, but could you please – please! - just for two seconds _not_ try to set me up with someone?"

"I just wanted to do you a favor!" Sam replied with his hands risen defensively.

"Yeah, well, I don't want favors! I mean I'm glad for your support and all that, but have you considered I just want to figure out what the hell happened in my life during those last weeks? And that I'm maybe old enough to choose my partners by myself? Thank you very much."

With that, Dean pushed past Sam and Jess and headed blindly for his car. Thank god they had come in separate ones.

He didn't notice the dark-haired, blue-eyed man that rushed right past him and greeted Sam and Jess.

He just drove off.

Later that day, when Sam returned to their flat, Dean didn't daunt him a look.

"Dean," Sam tried, but Dean just looked stubbornly at the TV. Where Jimmy was out and reporting from some shop down-town where a child had crawled into one of the machines you could pull stuffed animals out. At least he'd got the purple giraffe he wanted.

" _Dean,_ " Sam said again, more insistent this time.

"What?" Dean snapped back without looking at his little brother.

"I'm sorry," Sam mumbled meekly. "I won't set you up any more. I promise. I just want you to know that you really have all my support."

"I know that already," Dean replied with a huff, placably.

"Good. I should also say sorry from our wedding planner. He didn't want to upset you either."

That made Dean look up in confusion. "What's he gotta do with it?"

"Like I said, I told him about your latest life crisis and he could relate. He also likes Andy a lot."

Dean grumbled. "Next time tell him that I can care for my own love life."

"Will do. Listen, we're going ring shopping next week. You wanna come with us?" Sam asked.

"What, why do you need _me_ there?" Dean asked back, quite confused.

"You're my best man. And my brother. If you haven't figured it out yet, your opinion is kinda important to me."

Dean rubbed his hand over his eyes. "Sure. When is it?"

"Thursday."

"If we're going in the afternoon, that could work."

Thursday, as it turned out, was one long day at work. Dean was beat and slightly pissed when he came to the jeweler's that evening. Sam was already walking up and down the room with Jess trying to calm him down.

"Dean! There you are!" she said as soon as Dean stepped into the store.

He tried to catch his breath before he answered. "Jup. Sorry I couldn't make it earlier, I had like three cars to fix at once and pretty much by yesterday."

Sam only shot him an understanding smile. "Sure. Don't worry about it. But, you know, now you missed our wedding planner, again."

"Again?"

"Yes, he came to see us after we tried the cake. He said he noticed you storming past him, but you looked so furious that he didn't even dare to say hello."

"Oh," Dean coughed and scratched the back of his head. "Sorry, can't remember him."

"Anyway, he says hi. And he said you should help us choose which pair of these we should get," Sam explained, pointing at two pairs of rings laying on the counter in front of them. The jeweler was patiently waiting a few steps away, carefully listening for any requests they may have. "Jess and I like both."

Both pairs were silver – or white gold, Dean didn't really care – one pair pretty plain with only a small white crystal in the middle of the women's band, while the other pair was decorated with a chiseled, fine ornament around the length of it, a beautiful work of art by itself.

"Well, I'd go for the plain ones, but knowing you the other pair will probably suit you better," Dean answered visceral.

Jess began to laugh, but it came out rather mockingly.

"What?" Dean asked with a frown on his face.

"That's exactly what the wedding planner said," she chuckled. "And I mean word by word. Sure you don't-"

Dean shut her up with a roll of his eyes. "No."

"Well, then," Sam clapped his hands, effectively attracting the jeweler's attention. "We'll take these," he added and shoved the two rings with the ornaments towards the guy.

_Lucky for your Uncle Sam, he didn't bother me with the wedding crap for a few weeks after that. Truth be told, those were not the most glorious weeks I had. I didn't date or hook up, I was far from being okay with myself. Not even Gabriel was able to help me with that._

"So, you wanna go out some time again?" Gabriel said, nursing his beer as the two of them sat in the bar one other Thursday evening. "Although it'd be pretty cool if you wouldn't leave me there alone this time."

"You vanished into the back room with some hunk."

"Still, you left me."

"You still found your way home."

"I did, after spending an hour on Google maps, which drained my phone's battery, so that I couldn't even call a cab and had to take the bus from where that guy lived. Which was, just FYI, somewhere in the middle of nowhere!"

"Yeah, I'm not taking pity on you here, Gabe."

"But, as my best friend-"

"You're not my best friend, dude."

"- it is your responsibility to get me home at such occasions. And it is my responsibility as your best friend –"

" _Gabe._ "

"- to take you out and get your mind off things when you're sulking."

Dean rolled his eyes. "I'm not sulking."

Gabriel raised an eyebrow, unimpressed. "Yeah? Then what's it that you're doing here? Farting rainbows all over the place?"

"Jesus Christ," Dean spat out, shooting a bitchface of Sam's proportions Gabriel's way. "Will you just let it go for once? I feel like I'm having to say this to everyone! Stop trying to hook me up and for Christ's sake stop trying to stuff me into one of your stupid boxes! Yes, I'm bi, _no_ , that doesn't mean I'm living as promiscuous as you do."

"Woah," Gabriel said after a short moment of staring at Dean. "Where did that come from?"

"I-"

"And since when are you anything _but_ promiscuous?" Gabriel added with a frown, effectively interrupting Dean. "Aren't you the definition of that?"

Dean swallowed. Truth be told, he was. At least with all the girls in the last couple of years. "Maybe realizing… that I'm into guys as well changed me a bit more," he replied quietly.

Gabriel just stared at him some more. " _What?_ "

"Well, I know I suck at relationships with girls. Who knows if I suck at relationships with guys as well?"

"Oh, believe me when I say that someone always sucks at relationships with guys, and I bet you would," Gabriel said smugly, "Pun intended."

Dean facepalmed. "Tell me again why I'm friends with you?"

"Because I'm _awesome_! C'mon, up top!" Gabriel sing-songed and held his hand up for Dean to high-five it.

"Forget it."

Gabriel shrugged. "Looks like it's just you and me, buddy," he grinned, looking at his hand.

"That sounds vaguely dirty," Dean interjected dryly and took a gulp of his beer.

"Not that, Dean-O. Self-five!" Gabriel proclaimed then and slapped his own hand.

"You are so incredibly lame."

"Then what are you, huh?" Gabriel tilted his head, smirking.

"Dealing with a pre-midlife crisis?"

"I'd say afraid."

"… what."

"Isn't it obvious?" Gabriel stated, shaking his head. "You're afraid of accepting who you are."

"I'm completely accepting who I am. Doesn't mean I have to live like it immediately," Dean rolled his eyes.

"Aren't you curious?"

Dean had risen his beer bottle to his lips and set it down hard onto the table at that. "Of course I'm curious! Curious as hell, in fact! But I'm also not a teenager any more who would jump into just anybody's pants to lose their virginity. I know better than that."

"So, you're, what? Waiting for the one?" Gabriel mocked.

"What if I am, huh?"

"I'm just wondering, because that's not like you at all."

"Yeah, maybe it is. I just a feeling, you know," Dean said quietly, and strangely enough, it was the truth.

_Back then, I couldn't really nail down what it was, kids. I thought it was just a weird feeling because of my life had turned upside down. Apparently, there was more to that, though._

_I learned about it about a month later, when Sam and Jess had their wedding run-up._

_But at least they left me be and didn't try to hook me up with anyone._

"Are we ready?" the priest asked into the room just as Dean burst through the doors.

"Sorry," Dean quickly whispered to Sam as he reached the altar. "Work."

Sam just nodded, clearly relieved to see his brother. "'s okay. Go to your mark."

And Dean quickly made his way up to the priest, smiling apologetically. "Hi. Uhm, I'm the best man?"

The man only raised an eyebrow at Dean and went back to his book. "Well, then I think we can start."

He began to read, and while Sam already stood in front of the altar, Jess waited for her cue to walk up the aisle. Dean didn't really listen to what he said, just remembered that he had to hand them the rings as soon as they were done speaking their vows. Which was about all he really needed to know. The rest of the ceremony was way to chick-flick-y for him.

A few minutes later, when the father was busy closing the ritual, Dean noticed that the door to the small chapel that Sam and Jess chose was opened once again. All eyes in the room were drawn to the unexpected movement, but it was only Jimmy, raising his hand in apology. Jess shot a short smile at him and turned back to her soon-to-be husband. The priest went on.

Dean, on the other hand, found his eyes still drawn to Jimmy. Something was wrong. Not wrong in a bad way; just different. Something about Jimmy was different. His hair? No. Tousled as always, one way or another. The trench coat was also in place. Outwardly, he didn't look any different than else.

Dean shook his head slightly and tried to shake the weird feeling off. Surely he was just imagining things.

That's when the father clapped his hands. "Good job, everyone! I think that the ceremony will go just fine. It would just be nice if the best man here-" he scowled at Dean with, again, a risen eyebrow, "- would pay a little more attention."

"Sorry, father," Dean replied quietly and bent his head like a little kid getting reprimanded by his dad.

When everybody drifted apart and partly towards the door already, Jimmy was the first to come up to the altar.

"Oh, I'm glad you could make it," Jess said immediately and hugged him.

"Can we talk for a second?" Sam asked, and already lead Jimmy away, only turning towards Dean when he was a few feet away. "I'll see you at home, Dean!"

"Sure," Dean said and waved.

Right then, Jimmy turned his head as well and locked eyes with Dean.

Again, that weird feeling. Something was different about the way Jimmy looked, about the way he smiled at Dean and waved as a matter of goodbye.

Dean didn't have any time to dwell on it, though, because Gabriel was tapping his shoulder. "Hey big guy, can you give me a lift home? Sam took me here, but I guess he'll be busy for a little while longer and I really need to get home."

Nodding absent-mindedly, Dean mumbled, "Yeah, sure."

They left, and Dean drove straight home after dropping Gabriel off. That weird feeling still wouldn't leave him. Something was off, damnit, and it bugged him to no end. _I'm going crazy_ , Dean thought when he opened the door to the flat and dropped his keys into the bowl beside it.

Exhausted, he flopped down onto the couch in the living room, reflexively reaching for the remote and switching the TV on. Jimmy was on air, reporting from some-

Dean blinked. Twice.

Jimmy was on air.

In the middle of a report.

How could he have driven to the station and gotten ready for the news? Dean knew from enough of Jimmy's stories that it always took some time to get him ready. And it had been barely a ten minute drive from the chapel. There was no way-

 _Jep, I'm going crazy,_ Dean thought and laid down on the couch. Rubbing his eyes, he felt how sleep slowly overpowered him. Life, he decided, was too much for him to handle at the moment.

He woke up about two hours later, from his cell phone buzzing in his pocket. With a displeased groan, he managed to fumble it out of his jeans and saw that he had an unread message. From Jimmy. 'Bar?' it said.

'Yes, please. Now?' Dean answered.

'Sure. Meet me there.'

With another groan, Dean sat up and ran his hands over his face, trying to wake up completely. A beer would help, he was sure.

Two minutes later, Dean sat in their usual booth, one beer in front of him, one opposite of him, waiting for Jimmy.

"Hello, Dean," Jimmy's familiar voice greeted him as the other man sat down across the table.

"Hey, man," Dean said, still a bit sleepy.

"You look rather tired, if I may say," Jimmy said, and Dean looked closer at him then.

His voice sounded... like the deep voice he'd only used as a reporter. He also had that strange aura going on again. Dean frowned irritatedly, but answered, "Yeah, I just slept for two hours or so. Was pretty drained after that wedding run-up."

Jimmy huffed softly. "I am aware that these events tend to end up pretty stressing. I hope you recovered in the meantime?"

Dean had to blink. Jimmy sounded... not like himself. Maybe he was a bit off because he just returned from work? Did reporters have to express themselves like this? "Yeah, yeah, I did," Dean managed.

"So what did you think of the run-up?" Jimmy asked, taking a tentative gulp from his bottle.

"But you where there, why-?" Dean left the sentence unfinished, not yet knowing what was off.

"Oh, yes, of course, but I just wanted what you thought."

Dean swallowed another sip of his beer and shrugged. "Right. I think it'll be fine, not that I've got much experience with those things."

"In all honesty, I am much more looking forward to the reception. It's going to be a wonderful party," the edges of Jimmy's lips twitched upwards, and Dean noticed that he hadn't even smiled today. Which was weird as well. Huh.

"You've got quite some faith in the wedding planner, huh?"

"Yes, I do. He's a very capable acquaintance of mine."

Okay, so by now, Jimmy sounded almost ridiculous. Dean decided that he needed something more than just a beer.

"Hey, you want some scotch? Round's on me," he offered, fumbling for his wallet.

"I don't-" Jimmy began, but quickly stopped himself. He was getting weirder by the second. "Well, yes, sure."

"Great," Dean said smiling and went to Jo at the bar.

When he returned, Jimmy sat opposite of the table staring at his beer bottle. Dean placed the glass in front of him and flopped down.

"Cheers," he said, holding it towards the other man. They clinked glasses and Dean downed his shot at once. He immediately waved for Jo to refill their glasses. That is, after Jimmy sceptically drained his, too.

After a few moments of staring awkwardly at each other, Dean finally found the courage to ask. "So, what's up? You seem a bit off today."

Jimmy startled visibly, but shrugged it off and tried to sound nonchalant. "I can assure you, it's nothing. My working schedule is just exhausting."

"Yeah, I bet," Dean said.

If he hadn't known Jimmy, he'd say there was a completely different person sitting in front of him. But there he was, usual big blue eyes that eyed Dean hesitantly and tousled dark hair and trench coat. And that deep, rolling voice that Dean usually only heard on TV. If that was another side of Jimmy, he couldn't exactly say that he didn't like it.

"You seem rather uncomfortable, too. Are you alright?" Jimmy asked tentatively.

Dean nodded warily. "It's just the usual crap. Lot of work. Sammy getting married. Me in my pre-midlife crisis."

"Yes, I've heard- I mean, I see."

Dean tried not to let anything on and drowned another shot of whiskey. When he eyed Jimmy expectantly, he did so as well. Dean ordered another round and sighed deeply as soon as Jo was away. "I mean, I'm happy for Sam and Jess, they really do deserve this, and I know they'll make each other happy. But, between us, it feels so weird. I'm four years older than him and I got nothing."

"You shouldn't sell yourself short, Dean," Jimmy interjected quickly. The sound of his voice and the compliment sent a jolt of... something – down Dean's spine. He really should have eaten something before he got drunk with his friend. But, well. Another round of shots was emptied.

"It's just... I want a family, too, Jimmy. One of my own. Kids. A house. A dog. I don't know. And now I'm finding myself drawn to guys more than to chicks and how could that ever work out?" he let out a deep sigh and rubbed his temples with one hand.

"Well, there are enough possibilities offered nowadays. There's adoption and surrogate mothers, and you can always buy a house and a dog-"

"Not so much with the crappy salary I'm making."

"... so you're just dissatisfied with the situation as a whole?"

"Yeah," Dean huffed. "Pretty much. I'd wish I'd have known this sooner about myself. Would've made a lot of things easier."

"Maybe, maybe not. Consider high school."

Dean let out a bitter laugh. "That one not so much."

"See. I told you I could relate," Jimmy nodded, then lifted his shot glass to Dean. "Cheers, Dean."

And yeah, his name spoken in that deep voice did do things to Dean that he didn't want to specify in that moment. He was far from caring about the oddness surrounding Jimmy by that point. The alcohol slowly did its work, and Dean found himself soon pleasantly buzzed. Dean quickly found himself babbling, lost in tales about high school and Sam's earlier pranks and some anecdotes about their dad. Jimmy mostly just smiled secretively, but in the end, Dean had him chuckling at most of his tales. Again, highly unusual but also... Dean couldn't shrug it off. This side of Jimmy seemed rather adorable. Something Dean could really get used to.

But drinking whiskey shots the way they did ended their evening pretty soon. When Jo refused to give them any more shots and instead sent them upstairs, Dean grumbled. But Jo knew him by now, and truth be told, he was beat for the day. So he still grumbled, but stood up to get upstairs. And woah, the world was spinning. Not exactly what he had been planning on. Dean blinked before he noticed that Jimmy had the same problem.

Laughing quietly, Dean took Jimmy's arm around his shoulders and held him in a somewhat vertical position. Jimmy reflexively curled his arm around Dean's waist and followed him.

"Night," Dean called out to Jo and Ellen, noticing the older woman shaking her head at them. Dean only grinned.

They made their way up to the flat slowly. The stairs were kinda tricky, and by the time Jimmy stumbled for the fourth time and made some grunted, displeased noises, Dean looked over at him. "Jimmy, you alright?" he asked.

No reaction. Not even Jimmy turning his head towards Dean. But then again, they were plastered. So what.

Dean unlocked the door to the apartment, which proved rather difficult with Jimmy still hanging from his shoulder. He mumbled incoherent sentences against Dean's shoulder, even as Dean dragged him inside and let him slump down onto the sofa. Somehow, he managed to get the trench coat off his almost limp body, and found a blanket to toss over him.

"Jimmy?" Dean asked, not quite convinced that the other man was already asleep.

No reaction, again, even though Jimmy was wriggling on the couch, eyes on half-mast.

"Jimmy?" Dean said again, softer this time, and nudged Jimmy's shoulder lightly.

Blue eyes opened slowly and locked with Dean's, Jimmy's mouth lightly parted as he stared at him. It took a lot of Dean's willpower to not lean down and kiss him. They were friends, for crying out loud. Only friends. That tingling sensation in Dean's stomach had nothing to do there.

The side of Jimmy he had got to know tonight was making Dean considering his intentions towards him again. He sighed.

"Are you sure you're okay, Jimmy?" Dean asked. "Do you need something to-"

"'m not," Jimmy mumbled.

"What? Sorry, I didn't hear you, dude."

"I am not," Jimmy said, louder this time, with obvious exertion.

"What not? Not okay?"

"No... I'm not Jimmy," he mumbled, eyes slipping closed again. Seconds later, soft snores were heard in the living room of Dean's and Sam's apartment.

"Yeah, right," Dean snorted and went to bed himself.

The next morning, Jimmy was gone and Sam didn't ask what happened. He just brought Dean a glass of water and two Alka-Seltzer.

The wedding was two days later.

_"That sounds like you got drunk with Daddy, not with Uncle Jimmy." - "It was your Daddy, sweetie."_


	5. Chapter 5

**The year 2030**

_So, inevitably, the day of Sam's and Jess' wedding came. God knows I had no idea what was in store for me. Hell, I don't know if I would have even wanted to know. I can tell you, though, that it was one of the most confusing, most wonderful days of my life._

**The year 2006**

Sam stood in front of his bedroom mirror and ran his hands through his hair.

"You look fine, stop fidgeting," Dean said, for about the thousandth time.

"Excuse me for being a bit nervous, Dean," Sam grumbled.

"There's no need to be and you know it. Seriously, you're about to do the best thing you ever did in your whole life."

"I know..."

"Good, then-"

That moment, the door was opened, revealing Jimmy. "Sam, are you done?"

"Yes, Jimmy, he is," Dean answered instead of Sam and shot a short smile at his friend.

Suddenly, Sam turned around to the two of them, looking from Dean to Jimmy and back, a hesitant smile on his face. "Oh, uhm," Sam added, fumbling with his cufflinks now. "I think I need to clarify something. This is my brother Dean," Sam said, pointing at Dean who just looked at him as if he was retarded, "- and this is my wedding planner, Ca-"

"Castiel," the man who Dean had thought to be Jimmy said in his deep, gravelly voice and reached his hand out to him.

Dean shook it, confusion written all over his face. Sam was cackling. "Sorry that I didn't tell you sooner, but I wanted you to-"

"Sam! C'mon out here, we're about to start!" John Winchester's voice carried through the open door.

"Coming!" Sam yelled back, patting Dean on the shoulder on his way out.

The whole hustle left Dean completely baffled and staring after Sam. A hand on his elbow – Castiel's – had to yank him out of his daze. "I think we need to go, too," he said.

Blinking absent-mindedly, Dean followed them around the room. He needed a few seconds to process all that new info. Which, wow. When the hell...? How had he missed that?

Then he remembered how odd Jimmy had seemed two nights ago. And his unusual deep voice and his unusual way to express himself. So that meant-

What did it mean?

Just a lot of confusion for Dean. He felt like riding a roller coaster.

_Well, kids, I can't possibly tell you a lot about the wedding. You've seen the pictures, and yes, it was perfect and your grandma cried a lot and your dad did a really good job arranging all that. What I can tell you about, however, is what ran through my head all throughout the ceremony. I was a lot more busy with that than focusing on the ceremony anyway._

It took Dean most of the time of the wedding to comprehend what had truly happened. So there were two Jimmys out there. One of them he had a pretty bad physical, but not so much emotional attraction to. The other one, his twin brother or something, just as hot, was an enigma to him. The things Sam had said about him in all those months before the wedding slowly came back to mind; about how he could relate to his current life crisis, about him liking Andy, the little things he'd said. Knowing Sam, Dean was very aware of the fact that Castiel probably knew enough about Dean himself.

Also knowing that the guy was a wedding planner, plus the aforementioned facts brought Dean quickly to the conclusion that Castiel was most likely gay.

Which was at least something.

Dean had to force himself to focus on handing the rings over at the right moment, sign the papers he had to as best man, but truth be told, his eyes were mostly wandering. Drawn again and again to the guy that stood at the sidelines, away from family and friends, just to coordinate everything around himself. Wrapped up in his work like this, Dean had plenty of time to watch him without Castiel noticing.

What kind of name even was that?

His eyes where still resting on Castiel when, for the first time, the other man looked over as well and their eyes met. For a long moment, Dean involuntarily held his breath, just watched, didn't even blink, until Castiel smiled at him. It wasn't one of those face-splitting grins Jimmy did mostly. It was small, a bit lopsided, but Castiel's eyes crinkled at the corner and his blue eyes sparkled. The smile was genuine, Dean could tell, and it stirred up some long-forgotten feelings in his chest. He smiled back awkwardly, aware that he had been caught staring, but nonetheless just as heartfelt. Cas seemed like a nice guy, and Dean was intrigued.

Dean snapped back to reality then, because the music started to play and Sam and Jess made their way out of the chapel. As best man and the designated driver, Dean had to stay on their heels. At least he had refused to let them decorate his baby in red roses all over. Still, Gabriel had managed to tie a few cans to the back and the hood sported a small flower arrangement in white. Castiel had picked it out. And Dean couldn't even pretend that it was too cheesy for him. It was tasteful and it fit and his baby looked just right for the occasion.

_I don't think I even have to tell you kids that the reception was the much bigger event of the day. There was the lemon and walnut cake we had selected, and there was a band and – what am I even saying, as I've said, you've seen the pictures. Sam's and Jess' first dance was wonderful, obviously, and afterwards when everybody was encouraged to dance, that's where it began. Where I actually, really, met your father. You see, I was single, and apparently good boyfriend material, so quite some mothers shoved their daughters into my arms, too. It took us some time to actually get to talking._

Still, Dean's eyes kept returning to Castiel. He hurried across the room various times, arranging this and that, being busy with wedding planner stuff. And Dean just watched and ignored the various ladies' disapproving looks. Castiel was elegant, moving through the crowd like he wasn't even there, was nice and friendly and selected his words carefully. Dean wanted to talk to him, but every time a song was finished another woman stood before him, twisting her hair around her finger and just waited for being asked to dance. Gentleman that he was, Dean smiled and did so every time. And gritted his teeth and watched Castiel some more.

Until eventually, after one and a half hours, Dean caught a break. His feet hurt, the song was generic and nothing special, most of the people had already sat down for coffee again, and Castiel stood at the side of the dance floor. He was obviously on break, too, and Dean took a good chance if it was handed to him, hurting feet or not.

With a few steps, he stood in front of the blue-eyed man.

"I guess you're the guy I got drunk with two nights ago, then?" Dean asked straight ahead and grinned.

Castiel smiled back a bit shyly. "Considering the hangover I had to nurse yesterday, I was. And just so you know, I usually don't drink."

"And there I wondered what was wrong with Jimmy," Dean smiled widely.

"Well, in fact, there wasn't anything wrong with him. Jimmy just wanted me to meet you and offered to arrange a little... date. I know how you think of these arrangements, and I beg you to forgive Jimmy in this case. And I think I paid for it with yesterday's hangover."

"That you did," Dean smiled. Completely spontaneous, he held his hand out to Castiel. "You want to dance? It seems like no one ever asks the guy who arranged all of this so perfectly."

Castiel blinked, obviously surprised, but quickly took Dean's hand and let himself be pulled into Dean's arms as they entered the dance floor. "It's true. I rarely get asked to a dance. But then again, I'm mostly busy during receptions and I mostly decline women from the very start."

With a few sure movements, Dean placed his hand on Castiel's waist and led him confidently through the first steps. "And why is that?" he asked as they fell into rhythm with the music, a classic waltz.

A few catcalls from the side made Dean look around and spot Jimmy in the corner, grinning brightly. And Sam, waving and giving them a thumbs-up. Dean rolled his eyes. When his eyes returned to the man in his arms, Castiel smiled secretively. "Getting back to your question about women. I'm gay, I don't want to raise false hopes. And I'm here to work."

"I see," Dean said. "'nother question. No offense, but why is it that your twin has such a... normal name and you- well. Not to use some bad pick-up line here, but Castiel rather sounds like an angel or something."

Castiel smiled and hung his head down onto his chest. That was a question he was obviously asked a lot. "To make a long story short, my parents were quite unsure about the name of their child when my mother became pregnant. My father was very religious and wanted to have a name related to Christian Theology. My mother, however, rather wanted a more common name. And when it turned out that we were twins, they decided that each of them would name one of us. So because I turned out to be the second twin, my father got to name me. I was born on a Thursday, and therefore the angel of Thursday is my namesake."

"Apart from the fact that I wouldn't call that a short story-" Dean smirked and left the sentence unfinished. "Can I just call you Cas or something? It rolls a lot smoother off my tongue."

"If you want, Dean. By the way, it's really pleasant to finally, really meet you."

Right then, the song ended and the music became slower. A lot slower. On some unspoken mutual agreement, Dean and Castiel stayed together and just changed their pace.

"I gather Sam has already spilled his guts about me?" Dean sighed.

"He did, yes. And the rest you did for yourself two days ago. Has he told you about me in any way?" Castiel inquired calmly.

Dean shook his head and conveniently didn't react to the side note about their night out. "Not much, no. He dropped something like you could relate to my situation, and now that you're saying you're gay, I understand."

"Anything you want to know?"

"Yes. Why become a wedding planner?" Dean asked before releasing Castiel's hip and swinging him around in a pirouette, catching him in his arms when the other man returned. They turned quite a few heads everywhere, Dean noticed. He also noticed that Cas danced fluently and that they seemed to match each other's moves perfectly. It felt good. Dean felt a bit light-headed, even though he only had two beers and that was pretty much peanuts for him. All of it was weird and new, and on some level Dean knew what was going on – he just didn't want to realize it.

"If you can't marry in most states because you're gay, but you really enjoy watching weddings and people being happy, it's a recommended way of earning your money," Castiel answered simply. "You are a mechanic, is that right?"

"Yes, that's right. If you really like getting your hands dirty and work on your own where you can swear as much at lifeless parts of an engine as you want to, that's a recommended way to earn your money," Dean grinned.

When their eyes met this time, it was like a faint electric buzz ran along Dean's spine. Castiel was nice to talk to, also very handsome, and he had just the same plush pink lips as Jimmy. Which Dean knew exactly how they felt, being kissed and all that. And right now, the thing he wanted to do most was kiss Castiel senseless. He swallowed down the urge though. For the moment.

"Why are you single?" Dean asked, only noticing after asking how blunt and incoherent the question seemed. He felt heat rising up on his cheeks, which Castiel didn't seem to notice. Or hid I really well. "I mean- you're quite- uhm-" Dean tried to add, but got quickly interrupted.

"It seems like I just haven't met the right guy yet. I think I don't need to ask why you're single, do I?"

Dean smiled awkwardly. "Yeah, not really. It's still quite embarrassing, you know, only noticing it that late."

"It happens," Castiel shrugged it off.

Another song began to play. Something faster. Castiel quickly fell into the steps to a Rumba and Dean just went along, his hurting feet long forgotten. Conversation flowed so easily between them.

"Dealing with it is a whole 'nother part, though," Dean said, a bit melancholically. He realized he had taken down the mood quite a bit with that and quickly apologized. "But, uhm - sorry, I didn't want to-"

"Don't worry," Castiel replied with a sympathetic smile. "I think you shared a few of your struggles with me two days ago."

The smile still played around the edges of his lips and Dean decided he liked it.

"I guess I did, yeah." Dean took a deep sigh, quite breathless from the quick dancing. They both said nothing for the rest of the song, but it was comfortable. A rather quick set of steps, perfectly executed, earned him an appreciative nod from Castiel, and when the other man did one of those pirouettes he always did so fluently and elegantly, Dean grinned as well.

For some reason, Sam stepped up towards the band and asked for a song, Dean noticed from the corners of his eyes. He didn't care much.

"I like dancing with you," Castiel finally gasped when the song was finished.

"Yeah, right back at you," Dean coughed back, taking a deep breath. They grinned at each other, and Dean stated to himself that Castiel's grin was very different from Jimmy's. He couldn't point it down, but it was definitely different. And Castiel didn't grin as much as Jimmy did.

He liked it, though, seeing Castiel smile. "You should smile more," Dean said on a gut reaction.

"Why?" Castiel asked, a wide smile on his face.

The next song began, and the band had chosen a very slow one. _'Every rose has its thorn',_ a rock ballad Dean immediately recognized. Without hesitating, he wrapped his arms around Castiel's waist and pulled him into his chest. Castiel went willingly, that dazzling smile still on his lips.

Now that they were so close, Dean was again reminded that this was a man in his arms. Castiel had broad shoulders, hard muscles were flexing underneath Dean's hands on his back and he was tall; taller than your average women. He almost reached Dean's eye level and for a man Dean's height, that was quite tall. Castiel also had those stunning blue eyes that made Dean breathless.

Dean noticed that he still hadn't answered Castiel's question. "Because your smile is... I dunno, I just have the feeling you don't smile very often. And that's a pity, Cas."

It was the first time Dean actually chose to call Castiel by the nickname. Cas' eyes blinked shortly, but then he smiled even brighter. "And I like being called Cas," he said quietly.

"Can I ask you something?" Dean said after a few seconds of positive tension.

"Go ahead," Cas nodded.

"What do you want? Husband, kids, house, dog? Or a cat maybe?"

That secretive smile returned to Cas' lips. "All of it. Especially the husband and kids."

"Really?" Dean asked, breathlessly.

"Yes, why would I tell you otherwise?"

It was Dean's turn to smile. Cas watched him expectantly, head tilted to the side in such an adorable way that Dean couldn't restrain himself anymore. Heat and nervousness curled in his chest in a way they hadn't ever before. "Nothing, just... I'm sorry if I seem so unsure. You know, I never had a serious relationship or anything, but that's basically all that I want, too."

"That's not what matters, you know," Castiel said deliberately slowly, "The important fact is if you want to try. If you think you're ready for something serious." A deep look in Dean's eyes, then, very quiet and hushed, "Are you, Dean?"

Dean swallowed. But yes, he was. Ready and sure of that. So he nodded with a shaky smile. "Cas," he asked, his voice rough and broken, and he immediately felt Castiel leaning into him a bit more, "Can I kiss you?"

"Right here, in front of all these people?" Castiel chuckled, deeply, and Dean was again reminded of how much he preferred that deep voice to Jimmy's.

"I so do not care about that," Dean answered, huffing out a short laugh and feeling the tell-tale butterflies spreading and going crazy in his stomach. It felt like a haze, completely unreal, how his heart rate jumped up to a higher pace and Dean was breathless for a second.

"In front of your parents?" Cas asked with a mischievous smirk that Dean never thought he was able to pull off.

"They already met you. So plus point for you anyway."

Cas smiled warmly at that and without interrupting the soft swinging of their hips to the slow beat of the music, he pushed Dean down by his neck and kissed him. With a low, silent sigh, Dean matched the movements of his lips, kissed him back with all he could offer. It was so very different from kissing Jimmy.

If the truth really was in someone's kiss, Dean knew that this was it right then. This was what he had been waiting for, whom he had been waiting for. He was lost in the touch and smell of Cas all around him, and so happy because of it.

However, they were interrupted by loud clapping and cheering from the people around them, Sam and Jimmy in the front line as Dean noticed when he broke the kiss reluctantly. "Hey, go cheer on Jess and Sam, it's their big day," he said, but he was unable to wipe that wide smile off his face.

With a thud, Dean felt Castiel's head landing on his chest as he laughed softly. Then he bent down to kiss the top of that dark mop of hair.

_As you know, kids, gay marriage was only legal in a few states back then. So the reactions were mixed, and a few people were infuriated and 'disgusted' by our behavior. We didn't care and Sam calmed the waves single-handedly. And the rest, as they say, is history. But that is a story for a different day._

THE END


End file.
